


Very Grateful

by dontcryMasha



Category: Thief (Video Game Original Series)
Genre: Drabble, F/M, First Time, Garrett is kind of a pervert, Loss of Virginity, Older Man/Younger Woman, One Shot, Quickie, The Dark Project, nasty Garrett
Language: English
Status: Completed
Published: 2016-10-12
Updated: 2016-10-12
Packaged: 2018-08-22 03:30:02
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,924
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/8270929
Author URL: https://archiveofourown.org/users/dontcryMasha/pseuds/dontcryMasha
Summary: Any "expert" knows that Garrett had physical motivations to break Basso out of Cragscleft. Even after the plan went south, he wasn’t going to give up his pursuits.





	

**Author's Note:**

> A bulletin board was discussing the name of Basso’s sister, as far as TDP is concerned, and someone confidently came up with Gwendolyn. I don’t know if this is accurate, but for the sake of this fic, that’s what we’re sticking to.

 

 

“So...he's dead.”

Gwendolyn, Basso's little sister, was devastated to hear the news regarding her brother in Cragsclef. Garrett had made a special trip out of his way to let Basso out of prison, but his plan took an unfortunate twist and really mucked up his idea of a reward. There was still hope though, if he could play it cool and pretend to have sympathy.

“I'm real sorry to be the one breaking it to you. I was going to let him out while I was in there.”

Gwendolyn touched a handkerchief to her eyes and dabbed them gently. “Oh, Garrett. That's so sweet of you. I wish he had been able to leave.”

“Me, too.”

Garrett watched as Gwendolyn paced around her study slowly. It was day time, unusual for Garrett to be out and about, and the sunlight was coming through the soft curtains. It caught the emerald color in Gwendolyns dress, which hugged her curvy frame well.

“Are you going to be okay?” Asked Garrett. Gwendolyn turned around quickly and he diverted his eyes from her hips.

“I don't know, I really don't. This is hard for me to take.” Tears began rolling down her porcelain cheeks, shimmering in the daylight. Garrett did his best to keep eye contact and not let his vision wander to the cleavage staring at him. Many times had he offered to meet with Basso at his house just so he could feast his eyes on those young breasts.

“Will you be okay financially? Basso helped me out enough that I practically owe it to him to help you out.”

“Ah, Garrett, that's so sweet but he left a lot behind, and sales at the stand have been good lately. I think that's the least of my issues.” Gwendolyn managed to push a chuckle through her weepiness. “That's so typical of you, considering money before anything else.”

“Believe it or not, it's not always the first thing on my mind.”

She closed her wet eyes and smiled. “I'm sure,” she said softly, but then the smile faded. She gasped and began to cry again, much harder--so much that she had to sit down.

“Hey, hey,” Garrett coaxed. He slid next to her on the chaise lounge and offered his arm. She leaned right up into his embrace and sobbed against his chest. “Oh, Garrett! He was my support system! My everything!”

“Sh, its okay.” Garrett brought his other arm around her and pulled her small yet voluptuous frame against him. Inside, he was drooling. “I'm here. You'll make it through this.”

“Oh, I knoo-oow,” Gwendolyn sobbed. “It just feels impossible now. Aah!” She sat back and gazed at Garrett, her eyes red and filled with tears. “I appreciate your comforting words, I truly do, but for now I think I need to be alone.”

“No worries, I understand.” Garrett took his arms off of her as he cursed in his head. “If you need me again, just come by my place. You're welcome anytime. Remember, I'm here for you.”

* * *

Of course it didn't take long for Gwendolyn to show up. It was quite late but Garrett was luckily home. She knocked, announced herself and he let her come in. He offered to take her cloak off, revealing a black dress. The scooped neck was enticing. Did she mean it so?

“How've you been managing?” Garrett asked.

“Not well, as you can imagine.”

“Yeah. I can. Do you want a drink? I've got ale and maybe spiced wine.”

“No thank you, as I don't believe any alcohol could distract me from my pain.”

“You can take a seat if you want. Whatever will help, whatever makes you feel better.”

“Thank you, Garrett.”

She made her way to his tattered sofa and settled in, placing her thin hands into her lap. Garrett sat next to her but left space between them.

“Our parents died when we were young,” she explained, speaking quieter all of the sudden. “I don’t know if Basso told you that.”

“No.”

“You two were close, but he didn’t like telling people that. Don’t hold ill against him for that. I was 7 And he was 13. He raised me, Garrett. He was essentially my father.”

“I'm sorry. You're lucky that he was there. I never knew my parents and I didn't have siblings. At least, not that I know of.’

“Oh, Garrett!” Gwendolyn gasped, bringing both hands to her mouth. “I hadn't the slightest clue you were an orphan! That’s terribly sad.”

“Eh, I got over it.”

“I don't know how you did. Time, perhaps. You're so much older than me.”

Garrett chuckled. “Way to rub it in.”

“I'm sorry! I didn’t mean it that way! You are--you look good for your age. And you're strong.”

Garrett raised an eyebrow. “Yeah?” He detected a bit of color flushing to her cheeks. Maybe some blood was moving in him, too.

“I--I don't mean it that way. Garrett, I'm sorry. My mind isn't where it has been. This disaster with Basso is turning everything upside down.”

“You're fine. No need to apologize.” He grinned. “When I was your age--what is it, again?”

“Twenty. I'm only twenty and I have nothing to stand for.”

Garrett pushed his knees together a little and cracked his neck. He was twice her age, and he had started fantasizing about her before she was even eighteen. He didn't realize.

“You’ve got plenty to hold to your name, don’t worry about that.”

Gwendolyn began to sniff. She wiped her eyes on the back of her hand. Garrett moved in and took a tear away with his thumb. She watched him and smiled sadly. “Oh, Garrett,” she sighed. “What would I do without you? You've been so good for me and for no reason at all.”

“Basso was my friend, and the family of my friends is important to me.” In his head, Garrett was gagging. “I’ve got no problems being here for you. It's practically my duty to honor Basso.”

Tears rolling from her eyes, Gwendolyn gazed up at the man and slowly parted her lips. “Garrett…”

He would let her make the first move. That way he'd eliminate the chance of her calling him out for being a pervert who couldn't control his hands. He had perfect restraint. If anybody knew about the fruit of patience, it was him.

Gwendolyn moved forward and clasped both hands around Garrett's jaw. They were cold. Garrett gazed back and her, blinking slowly.

“Garrett,” she whispered once more before closing her eyes and placing a kiss on his lips. It was small and closed mouth, just a timid thing that was likely scared to be testing the waters.

“Is...that all right?” She asked hesitantly.

“More than all right,” Said Garrett. “And I can give you a lot more than that.”

“Oh, but…”

“Hmm?” His hips were trying to rock forward but he forced them still. It was bad enough that he was fighting a sticky semi.

“I don't know how to put this lightly,” Gwendolyn whispered.

“You aren’t married, right?”

“Goodness, no. Garrett!”

“Heh heh. Sorry. What is it?”

She winced and leaned right into his ear. “I'm a virgin.”

Garrett nearly creamed himself. She was young, sexy, the object of his nastiest fantasies for nearly four years and now, while she kissed him so gently, was shyly admitting her virginity. What a hard thing to resist.

Garrett opened his mouth and clicked his tongue once. He put his hands on her waist and smoothed down her hips. “I can be gentle,” he whispered huskily.

“Are you...sure? I'm scared.”

“Nothing to be scared of. I just gotta know that you really want it.”

She wrapped her arms around his shoulders and nuzzled against his face. “I do. I want you to take me.”

Once he had the go ahead, Garrett wasted no time. He pushed her down onto her back and plastered himself on top of her. She let out a gasp that was immediately muffled by a hot kiss. He gave her a run for her money by really snogging her soft lips, forcing his tongue between them turning his head. Gwendolyn closed her eyes and did her best to kiss back though she couldn't keep up well. Garrett pulled away suddenly and caught his breath.

“Too hard?” He huffed.

“N-no, it's wonderful.”

“Good.”

He sat up and pulled his top off, then ran a finger down the front of Gwendolyns dress. Her eyes lingered on Garrett's chest. “Aah, I know I said you are strong but I had no idea you were so toned.”

“Thanks,” was all Garrett said. “In my line of work, I have to be. Nothing cosmetic…” He was too preoccupied with the breasts he was seconds away from finally seeing. He tugged down the low cut neck and let one tit pop out. It was precisely as he had imagined it; round, plump and with the perfect pink nipple. He leaned down and sucked it between his lips.

“Nngh...G-Garrett…” Gwendolyn wriggled beneath his touch, bringing her arms around his shoulders once more. She gripped onto his bare back and bounced her body towards his.

“Horny little thing, aren'cha?” He whispered, looking up at her. “Let me get you out of this. I want to see your whole body.”

“Y-yes…but...does it have to be right here?”

“Where else?”

“The bedroom…”

“Oh. Sure. Yeah. That's fine.”

How sentimental.

They moved into Garrett's chambers, where he got out of his pants and Gwendolyn peeled her dress off. Finally, Garrett got to see her entire figure. She lay on her back, knees together but arms open, showing off her supple bosom. Her eyes wouldn't leave Garrett's crotch.

“First time you've seen a dick, I'm guessing.”

Gwendolyn nodded slowly. “Not just that,” she added in a tiny voice. “It's also...big. bigger than I thought they were.”

“Gwen, they can be all sorts of sizes.” He took his place straddling over her once more, hands on either side of her shoulders and hips against her legs. “Open up.”

“But...my area.”

“I'm going to fuck you, there's no way around me seeing that twat unless you change your mind.’

Bright red, Gwendolyn held her breath and let her legs fall open, showing off the most perfectly pink pussy Garrett could have dreamed of. Even better was how wet it was--it sparkled in the dim candlelight.

“Well, well, well. Look who's begging for it.”

Gwendolyn wriggled uncomfortably. “Do you have to look?”

“Yeah, and it looks good. Relax.”

“Is your penis going to fit?”

Garrett smirked. Such proper language. He put his hands on her knees to help spread then apart, then he rubbed his cock head against her moist lips. He could feel the heat radiating from her snatch.

“Feel good?” He whispered, rocking his hips lightly. Gwendolyn’s face was like a tomato.

“It is,” she whimpered. “Already. Very...very nice.”

“Great.”

He closed his eyes and nudged his way inside her. The moist hole was unbelievably tight and he had to really take his time or else it could hurt her badly. Her shaking fingers pressed into Garrett’s back harder, eyes quivering with mixed emotions. “G-Garrett…”

“Okay?” His voice cooed breathlessly as he dipped down to her face and touched their noses together. Gwendolyn gasped a few times, then closed her eyes and smiled.

“Y-yes...hng...I’m nervous. You’re so big.”

“You certainly know how to make a man feel good about himself,” Garrett chuckled. He nuzzled her nose to the side and kissed her lips as he eased his shaft deeper inside her. “You can put your legs around my waist if you want. That can help and it’ll give you more room to wiggle.”

“A-All right.”

She did just that, sliding her slender calves over Garrett’s hip bones, then crossed her legs together and pulled him to her more. Garrett laughed, raising his eyebrows. “Ooh,” he teased, “Getting greedy, aren’t we?”

“I like it,” she murmured. “I want all of you, even if it hurts.”

“We-ell, all right.” 

Garrett feigned apprehension. He let every inch of him slide inside, throbbing as he did so. Gwendolyn was so tight, so warm...Garrett threw his head back and let out a loud groan. “Damn!” he shouted. “That’s good!”

Gwendolyn had her lips pressed together tightly. Her eyes watched Garrett as he began to buck into her, picking up a decent rhythm. She was clearly overwhelmed, whimpering softly and tensing her legs.

“You like it?” Garrett moaned. He was almost drooling from the sensations of her virginity slipping away. His speed increased. Gwendolyn’s high pitched moans pressed through her quivering mouth. 

“It’s so good,” she cried. “It’s  _ so  _ good!”

In one swift motion, Garrett grabbed Gwendolyn around the waist and embraced her, letting their bodies rub together as he began humping at a rough speed. The young woman’s fingers were slipping slightly in the perspiration that steadily appeared on Garrett’s back.

“Naaah!” Gwendolyn moaned. “Oh,  _ my! _ ”

Toes curling, heart racing, she let her breasts smother Garrett’s chest. Soft hair tickled her nipples and she giggled.

“Wha?” Garrett laughed through trembling breaths. His cock was throbbing hard. Holding back his orgasm was getting nearly impossible, and Gwendolyn’s helpless moans were not helping.

“ _ It’s so nice _ ,” she uttered, opening her eyes to meet Garrett’s gaze. “I think---nnyeeh---it’s so  _ wonderful _ , Garrett! Gaah!!”

“You want to come? I bet you do. Here. Turn over. C’mon.”

“Huh?”

“Turn over.”

Garrett slowed his thrusts until they stopped. His heart was beating heavy in time with his raspy breathing. Gwendolyn seemed caught off guard. She wiggled her legs around him.

“ _ Turn over _ ,” he repeated, darker this time.

“I’m sorry!” The girl slipped off of his body and rolled onto her hand and knees. “Like this, I’m sure?”

“Just like that...”

He mounted her rear, grabbing her hips and pulling that fabulous pussy back over his cock. A shiver went up his spine as he was engulfed by the tight warmth once more. Feeling the better angle right away, Gwendolyn’s eyes shot open and she let out a loud moan.

“Oh,  _ Garrett! _ ” She yelled.

“You think it’s good right now? Hold onto something.”

“Huh? What do you--”

Gwendolyn’s voice cracked as she was cut off. Garrett gripped her hard and began pummeling that poor rearend. She immediately began moaning--shouting-- _ screaming _ from the incredibly angle he was getting. 

“Ooh! G-Garrett! Nnnh--aaahh!”

“Just like that,” Garrett repeated in a whisper, watching her ass bounce up against his hips. Sweat was beading down his forehead. He grunted continuously, licking his lips and feeling pretty good about himself. “ _ Thank you, Basso _ ,” he thought.

Gwendolyn was gripping his sheets in desperation. Her whole body convulsed. The sensations were overwhelming. Garrett was inside her--deep inside. His cock was  _ huge  _ and making her feel better than anything ever had prior to the experience. Her eyes rolled back into her head and she moaned something fierce. Garrett took the plunge and wrapped his arms around her, arching his whole body around her so that his chest was plastered against her back. He grabbed and groped at her pussy, rubbing the meaty mess with fervor.

“Gaah!!! G-Garrett! I--I--Oh! OH! What!!”

He took one hand away from her crotch and instead pushed the back of her head down into the pillows. Her desperate moans were muffled but that didn’t stop her. She was tightening up so much that Garrett knew exactly what was going on. He rode out her orgasm furiously, then just as he could barely stand it anymore, he pulled out and shot his load across her spine.

“Gaah….aaah...how…”

Gwendolyn collapsed onto the bed, twitching a bit but smiling into the pillow. Garrett chuckled. He turned around and flopped onto his bed then motioned for the girl to join him. She barely managed to crawl up and onto his chest. One shaking hand made it up near her face and she slowly traced circles in his chest hair.

“Good for you?” Garrett asked.

“Much so.” She looked up at him and smiled. A flood of color was filling her cheeks. Garrett bit his lower lip, trying to fight back a cheeky grin. “What?”

“Nothing,” said Garrett. “Are you feeling better?”

“A little bit, I must admit.” She closed her eyes shyly. “It seems wrong.”

“Why?”

“To be grieving and then do this.’

Garrett shrugged. He put an arm around her. “Everybody needs to get fucked sometimes.”

“I suppose you’re right.”

“And this is just the beginning for you. Imagine all the men you’re going to go around the block with.”

Gwendolyn’s eyes opened once more and she gazed up at Garrett sadly. “I...how many? I don’t know if I want that.”

“Sure you do,” Garrett said, nudging her. “Like you said, I’m getting old. Think about how good it’ll be with a young guy.”

“Eh…”

“ _ Damn _ ,” Garrett thought. He was kicking himself now. A man with his thieving experience should have known better--stealing a woman’s virginity always meant stealing her heart, even if he didn’t want to. There was a long road ahead of him. One he couldn’t pay off even if HE wanted to (though he wouldn’t). But hey, before he managed to chase her off without breaking her heart too much, he might get to pound that ass a few more times--because Garrett always gets what he wants and slips away from what he doesn't.


End file.
